CA2671770A1 - Intermediaire innovant et procede utile dans la preparation de {2-[1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-4-yl-1h-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chlorophenyl)-methanone - Google Patents
Intermediaire innovant et procede utile dans la preparation de {2-[1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-4-yl-1h-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chlorophenyl)-methanone Download PDFInfo
- Publication number
- CA2671770A1 CA2671770A1 CA002671770A CA2671770A CA2671770A1 CA 2671770 A1 CA2671770 A1 CA 2671770A1 CA 002671770 A CA002671770 A CA 002671770A CA 2671770 A CA2671770 A CA 2671770A CA 2671770 A1 CA2671770 A1 CA 2671770A1
- Authority
- CA
- Canada
- Prior art keywords
- pyridin
- chlorophenyl
- methanone
- hydroxy
- vinyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 19
- CAVRKWRKTNINFF-UHFFFAOYSA-N [2-[1-[[3,5-bis(trifluoromethyl)phenyl]methyl]-5-pyridin-4-yltriazol-4-yl]pyridin-3-yl]-(2-chlorophenyl)methanone Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(CN2C(=C(N=N2)C=2C(=CC=CN=2)C(=O)C=2C(=CC=CC=2)Cl)C=2C=CN=CC=2)=C1 CAVRKWRKTNINFF-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 230000008569 process Effects 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- GMNRLJOAZMNQMK-UHFFFAOYSA-N (2-chlorophenyl)-[2-(2-hydroxy-2-pyridin-4-ylethenyl)pyridin-3-yl]methanone Chemical compound C=1C=NC=CC=1C(O)=CC1=NC=CC=C1C(=O)C1=CC=CC=C1Cl GMNRLJOAZMNQMK-UHFFFAOYSA-N 0.000 claims abstract description 14
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 claims abstract description 14
- BCYBZAQWIMJEOI-UHFFFAOYSA-N benzoic acid (2-chlorophenyl)-[2-(2-hydroxy-2-pyridin-4-ylethenyl)pyridin-3-yl]methanone Chemical compound OC(=O)C1=CC=CC=C1.C=1C=NC=CC=1C(O)=CC1=NC=CC=C1C(=O)C1=CC=CC=C1Cl BCYBZAQWIMJEOI-UHFFFAOYSA-N 0.000 claims abstract description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 31
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 18
- 229940011051 isopropyl acetate Drugs 0.000 claims description 14
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 14
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 8
- JKGHUBCPWOLOFQ-UHFFFAOYSA-N 1-(azidomethyl)-3,5-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(CN=[N+]=[N-])=CC(C(F)(F)F)=C1 JKGHUBCPWOLOFQ-UHFFFAOYSA-N 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000011877 solvent mixture Substances 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 abstract description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 38
- 239000000243 solution Substances 0.000 description 37
- 239000000203 mixture Substances 0.000 description 25
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000007787 solid Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- MPTVNPMFAZVTJG-UHFFFAOYSA-N 2-(benzenesulfonyl)pyridine Chemical compound C=1C=CC=NC=1S(=O)(=O)C1=CC=CC=C1 MPTVNPMFAZVTJG-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- CQFZPZLDLNMGAW-UHFFFAOYSA-N [2-(benzenesulfonyl)pyridin-3-yl]-(2-chlorophenyl)methanone Chemical compound ClC1=CC=CC=C1C(=O)C1=CC=CN=C1S(=O)(=O)C1=CC=CC=C1 CQFZPZLDLNMGAW-UHFFFAOYSA-N 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- 239000000047 product Substances 0.000 description 4
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- OINTXXMBRBLMHH-UHFFFAOYSA-N 1-(chloromethyl)-3,5-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(CCl)=CC(C(F)(F)F)=C1 OINTXXMBRBLMHH-UHFFFAOYSA-N 0.000 description 3
- WMQUKDQWMMOHSA-UHFFFAOYSA-N 1-pyridin-4-ylethanone Chemical compound CC(=O)C1=CC=NC=C1 WMQUKDQWMMOHSA-UHFFFAOYSA-N 0.000 description 3
- 101150041968 CDC13 gene Proteins 0.000 description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
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- 238000003786 synthesis reaction Methods 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 108091006629 SLC13A2 Proteins 0.000 description 2
- 206010041250 Social phobia Diseases 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 102000007124 Tachykinin Receptors Human genes 0.000 description 2
- 108010072901 Tachykinin Receptors Proteins 0.000 description 2
- 206010047700 Vomiting Diseases 0.000 description 2
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- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 2
- 239000003471 mutagenic agent Substances 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- KFPMDNNVMQLXCF-UHFFFAOYSA-N (2-chlorophenyl)-[2-(2-hydroxy-2-pyridin-4-ylethenyl)pyridin-3-yl]methanone phosphoric acid Chemical compound P(=O)(O)(O)O.ClC1=C(C=CC=C1)C(=O)C=1C(=NC=CC1)C=C(C1=CC=NC=C1)O KFPMDNNVMQLXCF-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- RVWUHFFPEOKYLB-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-oxidopiperidin-1-ium Chemical compound CC1(C)CCCC(C)(C)[NH+]1[O-] RVWUHFFPEOKYLB-UHFFFAOYSA-N 0.000 description 1
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 1
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 1
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 102000003141 Tachykinin Human genes 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 208000000921 Urge Urinary Incontinence Diseases 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- -1 [2-[1-[[3,5-bis(trifluoromethyl)phenyl]methyl]-5-(4-pyridinyl)-1H-1,2,3-triazol-4-yl]-3-pyridinyl] ( 2-chlorophenyl)- Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
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- 230000008901 benefit Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
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- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940126534 drug product Drugs 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
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- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- 238000010949 in-process test method Methods 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 208000024714 major depressive disease Diseases 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- XBRSNMYZHZKDSW-UHFFFAOYSA-N n-(4-hydroxyphenyl)thiophene-2-carboxamide Chemical compound C1=CC(O)=CC=C1NC(=O)C1=CC=CS1 XBRSNMYZHZKDSW-UHFFFAOYSA-N 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000007339 nucleophilic aromatic substitution reaction Methods 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 230000020341 sensory perception of pain Effects 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- WCFMYNWLLNSYBH-UHFFFAOYSA-N sodium 1-(azidomethyl)-3,5-bis(trifluoromethyl)benzene azide Chemical compound [N-]=[N+]=[N-].[Na+].N(=[N+]=[N-])CC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F WCFMYNWLLNSYBH-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- CGRKYEALWSRNJS-UHFFFAOYSA-N sodium;2-methylbutan-2-olate Chemical compound [Na+].CCC(C)(C)[O-] CGRKYEALWSRNJS-UHFFFAOYSA-N 0.000 description 1
- 238000010950 spiking study Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
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- 108060008037 tachykinin Proteins 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 206010046494 urge incontinence Diseases 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 230000002455 vasospastic effect Effects 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A61P13/10—Drugs for disorders of the urinary system of the bladder
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- A—HUMAN NECESSITIES
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Hospice & Palliative Care (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87085106P | 2006-12-20 | 2006-12-20 | |
| US60/870,851 | 2006-12-20 | ||
| PCT/US2007/086319 WO2008079600A1 (fr) | 2006-12-20 | 2007-12-04 | Intermédiaire innovant et procédé utile dans la préparation de {2-[1-(3,5-bis-trifluorométhyl-benzyl)-5-pyridin-4-yl-1h-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chlorophényl)-méthanone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2671770A1 true CA2671770A1 (fr) | 2008-07-03 |
| CA2671770C CA2671770C (fr) | 2015-09-15 |
Family
ID=39273082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2671770A Active CA2671770C (fr) | 2006-12-20 | 2007-12-04 | Intermediaire innovant et procede utile dans la preparation de {2-[1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-4-yl-1h-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chlorophenyl)-methanone |
Country Status (22)
| Country | Link |
|---|---|
| US (4) | US8772496B2 (fr) |
| EP (1) | EP2121610B1 (fr) |
| JP (1) | JP5443168B2 (fr) |
| KR (1) | KR20090081028A (fr) |
| CN (1) | CN101568523A (fr) |
| AU (1) | AU2007337255A1 (fr) |
| BR (1) | BRPI0721069A2 (fr) |
| CA (1) | CA2671770C (fr) |
| DK (1) | DK2121610T3 (fr) |
| EA (1) | EA200970604A1 (fr) |
| EC (1) | ECSP099441A (fr) |
| ES (1) | ES2471990T3 (fr) |
| HR (1) | HRP20140613T1 (fr) |
| IL (1) | IL198775B (fr) |
| MX (1) | MX2009006636A (fr) |
| NO (1) | NO20092370L (fr) |
| PL (1) | PL2121610T3 (fr) |
| PT (1) | PT2121610E (fr) |
| RS (1) | RS53386B (fr) |
| SI (1) | SI2121610T1 (fr) |
| WO (1) | WO2008079600A1 (fr) |
| ZA (1) | ZA200903578B (fr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20090081028A (ko) * | 2006-12-20 | 2009-07-27 | 일라이 릴리 앤드 캄파니 | ｛2-[1-(3,5-비스-트리플루오로메틸-벤질)-5-피리딘-4-일-1ｈ-[1,2,3]트리아졸-4-일]-피리딘-3-일｝-(2-클로로페닐)-메타논의 제조에 유용한 신규한 중간체 및 방법 |
| US10098859B2 (en) | 2012-09-05 | 2018-10-16 | Amri Ssci, Llc | Cocrystals of p-coumaric acid |
| WO2016141341A1 (fr) | 2015-03-04 | 2016-09-09 | Vanda Pharmaceuticals Inc. | Procédé de traitement avec tradipitant |
| WO2017031215A1 (fr) * | 2015-08-17 | 2017-02-23 | Eli Lilly And Company | Procédé d'élaboration d'un antagoniste des récepteurs nk-1 contenant de la pyridine |
| BR112020004964A2 (pt) | 2017-09-13 | 2020-09-15 | Vanda Pharmaceuticals Inc. | método que consiste em administrar uma quantidade de tradipitant eficaz, aperfeiçoamento, método aperfeiçoado para tratar um paciente que sofre de prurido ou dermatite atópica com tradipitant, e, métodos para tratar um paciente com prurido ou dermatite atópica, para selecionar e para determinar uma dosagem de tradipitant eficaz, para determinar que um paciente tem probabilidade de responder ao tratamento de dermatite atópica com tradipitant e para identificar um paciente. |
| MX2020005167A (es) | 2017-11-17 | 2020-08-20 | Vanda Pharmaceuticals Inc | Metodo para el tratamiento de enfermedades gastrointestinales con tradipitant. |
| US10821099B2 (en) | 2018-09-28 | 2020-11-03 | Vanda Pharmaceuticals Inc. | Use of tradipitant in motion sickness |
| WO2020117811A1 (fr) | 2018-12-03 | 2020-06-11 | Vanda Pharmaceuticals Inc. | Méthode de traitement avec le tradipitant |
| EP4125811A1 (fr) * | 2020-03-26 | 2023-02-08 | Vanda Pharmaceuticals Inc. | Traitement d'une infection des voies respiratoires inférieures avec du tradipitant |
| WO2023019084A1 (fr) | 2021-08-12 | 2023-02-16 | Vanda Pharmaceuticals Inc. | Traitement de l'accommodation gastrique avec du tradipitant |
| WO2024138040A1 (fr) | 2022-12-21 | 2024-06-27 | Vanda Pharmaceuticals Inc. | Méthodes de traitement par tradipitant |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2483159C (fr) * | 2002-04-26 | 2010-08-10 | Eli Lilly And Company | Derives de triazole en tant qu'antagonistes des recepteurs de la tachykinine |
| PT1675846E (pt) * | 2003-10-24 | 2010-04-20 | Lilly Co Eli | Novas formas cristalinas de {2-[1-(3,5-bis-trifluorometilbenzil)-5- iridin-4-il-1h-[1,2,3]triazol-4-il]-piridin-3-il}-(2-clorofenil)-metanona |
| WO2006083711A1 (fr) * | 2005-02-01 | 2006-08-10 | Eli Lilly And Company | Antagonistes du recepteur de la tachykinine |
| KR20090081028A (ko) * | 2006-12-20 | 2009-07-27 | 일라이 릴리 앤드 캄파니 | ｛2-[1-(3,5-비스-트리플루오로메틸-벤질)-5-피리딘-4-일-1ｈ-[1,2,3]트리아졸-4-일]-피리딘-3-일｝-(2-클로로페닐)-메타논의 제조에 유용한 신규한 중간체 및 방법 |
-
2007
- 2007-12-04 KR KR1020097012894A patent/KR20090081028A/ko not_active Application Discontinuation
- 2007-12-04 EA EA200970604A patent/EA200970604A1/ru unknown
- 2007-12-04 AU AU2007337255A patent/AU2007337255A1/en not_active Abandoned
- 2007-12-04 PT PT78651379T patent/PT2121610E/pt unknown
- 2007-12-04 US US12/515,794 patent/US8772496B2/en active Active
- 2007-12-04 WO PCT/US2007/086319 patent/WO2008079600A1/fr active Application Filing
- 2007-12-04 ES ES07865137.9T patent/ES2471990T3/es active Active
- 2007-12-04 JP JP2009543027A patent/JP5443168B2/ja active Active
- 2007-12-04 PL PL07865137T patent/PL2121610T3/pl unknown
- 2007-12-04 DK DK07865137.9T patent/DK2121610T3/da active
- 2007-12-04 MX MX2009006636A patent/MX2009006636A/es active IP Right Grant
- 2007-12-04 RS RS20140349A patent/RS53386B/en unknown
- 2007-12-04 EP EP07865137.9A patent/EP2121610B1/fr active Active
- 2007-12-04 SI SI200731483T patent/SI2121610T1/sl unknown
- 2007-12-04 CA CA2671770A patent/CA2671770C/fr active Active
- 2007-12-04 CN CNA2007800466993A patent/CN101568523A/zh active Pending
- 2007-12-04 BR BRPI0721069-8A patent/BRPI0721069A2/pt not_active Application Discontinuation
-
2009
- 2009-05-14 IL IL198775A patent/IL198775B/en active IP Right Grant
- 2009-05-22 ZA ZA200903578A patent/ZA200903578B/xx unknown
- 2009-06-17 EC EC2009009441A patent/ECSP099441A/es unknown
- 2009-06-22 NO NO20092370A patent/NO20092370L/no not_active Application Discontinuation
-
2014
- 2014-03-27 US US14/227,857 patent/US20140206877A1/en not_active Abandoned
- 2014-06-27 HR HRP20140613TT patent/HRP20140613T1/hr unknown
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2015
- 2015-11-10 US US14/937,051 patent/US9708291B2/en active Active
-
2017
- 2017-06-15 US US15/623,550 patent/US10035787B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US20100056795A1 (en) | 2010-03-04 |
| JP5443168B2 (ja) | 2014-03-19 |
| PT2121610E (pt) | 2014-06-25 |
| AU2007337255A1 (en) | 2008-07-03 |
| PL2121610T3 (pl) | 2014-09-30 |
| ES2471990T3 (es) | 2014-06-27 |
| ECSP099441A (es) | 2009-07-31 |
| IL198775B (en) | 2018-08-30 |
| EP2121610B1 (fr) | 2014-04-02 |
| US8772496B2 (en) | 2014-07-08 |
| US20140206877A1 (en) | 2014-07-24 |
| DK2121610T3 (da) | 2014-06-30 |
| WO2008079600A1 (fr) | 2008-07-03 |
| EP2121610A1 (fr) | 2009-11-25 |
| BRPI0721069A2 (pt) | 2014-02-04 |
| ZA200903578B (en) | 2010-07-28 |
| RS53386B (en) | 2014-10-31 |
| CA2671770C (fr) | 2015-09-15 |
| US20170283394A1 (en) | 2017-10-05 |
| JP2010513546A (ja) | 2010-04-30 |
| NO20092370L (no) | 2009-09-16 |
| KR20090081028A (ko) | 2009-07-27 |
| IL198775A0 (en) | 2010-02-17 |
| EA200970604A1 (ru) | 2009-10-30 |
| HRP20140613T1 (hr) | 2014-08-15 |
| US9708291B2 (en) | 2017-07-18 |
| US10035787B2 (en) | 2018-07-31 |
| CN101568523A (zh) | 2009-10-28 |
| MX2009006636A (es) | 2009-06-30 |
| US20160060250A1 (en) | 2016-03-03 |
| SI2121610T1 (sl) | 2014-08-29 |
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